Ethyl Acetate → HCID 86668006, compound

HRID 474032Notes

Reaction equation

HRID 474032 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=O)[CH3:9])[CH:5]=[CH:4][CH:3]=1.[C-]#N.[K+].[C:14](=[O:17])([O-])[O-].[NH4+:18].[NH4+:19].CCO[C:23](C)=[O:24]>C(O)C.O.O.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[N:7]=[C:6]([C:8]2([CH3:9])[NH:19][C:23](=[O:24])[NH:18][C:14]2=[O:17])[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 112985782-Acetyl-6-bromopyridine

Product 1

HCID 86668006HCID 86668006, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(6-bromo-pyridin-2-yl)-ethanone (CAS 49669-13-8, 8.75 g, 43.7 mmol) and potassium cyanide (4.27 g, 65.6 mmol) in ethanol/water (40.0/26.7 ml) was added ammonium carbonate (21.02 g, 219.0 mmol). The reaction mixture was stirred in an autoclave at 100° C. for 17 h, then diluted with H2O, 1M aq. NaHCO3 soln. and EtOAc. The phases were separated and the aq. phase was reextracted with EtOAc, Et2O and DCM. The combined org. phases were dried over Na2SO4, filtered and concentrated to leave the title compound as a pale white solid that was used in the next step without further purification. HPLC RtH4=0.62 min; ESIMS: 270, 272 [(M+H)+]; 1H NMR (400 MHz, DMSO-d6): δ 10.86 (br s, 1H), 8.48 (s, 1H), 7.81 (m, 1H), 7.64 (d, 1H), 7.57 (d, 1H), 1.68 (s, 3H).

Workup

  1. customThe phases were separated
  2. dry with materialphases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-eb77815a247e4118a6ae550c8564aa19
Source dataset
uspto-grants-2014_01
Patent number
US08637508B2

Reaction notes

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